Potassium Carbonate → Ethyl 4'-[(1R)-1-(methylamino)-2-(4-morpholinyl)ethyl]-4-biphenylcarboxylate

Participants

Reaction Conditions

Reaction Steps

[(1R)-1-(4-Bromophenyl)-2-(4-morpholinyl)ethyl]methylamine (100 mg, 0.29 mmol) was dissolved in EtOH (5 mL) at room temperature with magnetic stirring. The resulting solution was treated with {4-[(ethyloxy)carbonyl]phenyl}boronic acid (62.9 mg, 0.32 mmol) followed by K2CO3 (122.3 mg, 0.88 mmol) and PdCl2(dppf)2·CH2Cl2 (12.0 mg, 0.015 mmol). The reaction mixture was maintained at 80° C. for 16 h. The reaction mixture was cooled to room temperature and then filtered through celite. The filtrate was concentrated and then partitioned between EtOAc and brine. The organic layer was dried over MgSO4, filtered and then concentrated. The residue was purified by silica gel chromatography (40 g Redisep column, silica, 40 um, 60 Å, 40 mL/min, A: MeOH (with 10% NEt3), B: CH2Cl2, A: 2% for 20 min, 5% for 20 min, detection at 254 nm) to give the title compound as a yellow oil (59.7 mg, 48% yield). MS (ES) m/e 369 [M+H]+.

Provenance & Evidence